93528-45-1

Basic information

• Product Name: dl-2,3-bis-2,3-butanediol
• Synonyms: dl-2,3-bis-2,3-butanediol
• CAS NO: 93528-45-1
• Molecular Weight: 378.314
• Mol File: 93528-45-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: dl-2,3-bis-2,3-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: dl-2,3-bis-2,3-butanediol(93528-45-1)
• EPA Substance Registry System: dl-2,3-bis-2,3-butanediol(93528-45-1)

Safety Data

• Hazardous Substances Data: 93528-45-1(Hazardous Substances Data)

Upstream product

• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 

Relevant articles and documents

CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

Light-enabled metal-free pinacol coupling by hydrazine

Efficient carbon-carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C-C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N2 and H2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.

Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light

Ketyl radical and amino radical anions, valuable reactive intermediates for C-C bond-forming reactions, are accessible through a C=O/C=NR umpolung. However, their utilization in catalysis remains largely underdeveloped owing to the high reduction potential of carbonyl compounds and imines. In the context of photoredox catalysis, tertiary amines are commonly employed as sacrificial co-reducing agents. Herein, an additional role of the amine is proposed, in which it is essential for the organocatalytic substrate activation. The combination of photoredox catalysis and carbonyl/imine activation enables the reductive coupling of aldehydes, ketones, and imines under mild reaction conditions.